There has been significant research on the synthesis and development of new energetic materials to meet the needs of U.S. Department of Defense. It is in this context that research has focused on a promising melt-castable energetic material 3,4-Bis(4-nitro-1,2,5-oxadizaol-3-yl)-1,2,5-oxadiazole-N-oxide (DNTF). Synthetic methods for preparing DNTF mainly involve treating 4-amino-3-chlorocarbohydroxymoyl-1,2,5-oxadiazole (chloro oxime) (1) with a base followed by extractive work-up to produce 3,4-bis (aminofurazano) furoxan (furoxofurazane) (2). The resulting furoxofurazane is further oxidized to produce DNTF (4).
Alternative methods have been explored to prepare a DNTF precursor by reacting 4-amino-3-chlorocarbohydroxymoyl-1,2,5-oxadiazole (chloro oxime)(1) with NaNO2 and an acid to convert the amino group in chloro oxime (1) into the corresponding nitro group in, 3-chlorocarbohydroxymoyl-4-nitro-1,2,5-oxadiazole (3). These experiments, however, were unsuccessful. Thus, a need exists for preparing DNTF using alternative methods. Disclosed herein is a novel method for synthesizing 3-chlorocarbohydroxymoyl-4-nitro-1,2,5-oxadiazole, an intermediate useful for the preparation of DNTF.